Dioxazinyl-Substituted Thienylsulphonylaminocarbonyl Compounds

Abstract

The invention relates to novel substituted thienylsulfonylaminocarbonyl compounds of the formula (I), in which R, Het and R 5 to R 8 are as defined in the description, to processes and intermediates for their preparation and to their use as herbicides.

1 . A compound of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which
 Het is 
 
     
       
         
         
             
             
         
       
       A is nitrogen or a CH grouping, 
       R is hydrogen, cyano, nitro, halogen, is in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms in the alkyl group, or is in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group, 
       R 1  is hydrogen, is halogen, is in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or is in each case optionally cyano-, halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy, 
       R 2  is hydrogen, is halogen, is in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or is in each case optionally cyano-, halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy, 
       R 3  is hydrogen, hydroxyl, amino, cyano, is C 2 -C 10 -alkylideneamino, is optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl- or C 1 -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, is in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, is in each case optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy- or C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, is alkenyloxy having 3 to 6 carbon atoms, is dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, is in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C 1 -C 4 -alkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or is in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl- and/or C 1 -C 4 -alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety. 
       R 4  is hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, is optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl- or C 1 -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, is in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, is in each case optionally fluorine-, chlorine-, cyano-, C 1 -C 4 -alkoxy- or C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, is alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group, is dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, is in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C 1 -C 4 -alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or is in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl-, C 1 -C 4 -alkoxy- and/or C 1 -C 4 -alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, and 
       R 5 , R 6 , R 7  and R 8  independently of one another are hydrogen, halogen, cyano or thiocyanato or are in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case 1 to 3 carbon atoms in the alkyl moiety, 
       or a salt of a compound of the formula (I). 
     
   
   
       2 . The compound as claimed in  claim 1 , wherein
 R is hydrogen, cyano, fluorine, chlorine, bromine, is in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or is in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy,   R 1  is fluorine, chlorine, bromine, iodine, or is in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,   R 2  is fluorine, chlorine, bromine, iodine, or is in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,   R 3  is hydrogen, hydroxyl, amino, is in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, is in each case optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl or butynyl, is in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, is propenyloxy or butenyloxy, is dimethylamino or diethylamino, is in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or is in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl,   R 4  is hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, is in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, is in each case optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, is in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetylamino or propionylamino, is propenyloxy, butenyloxy, ethynyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, is dimethylamino, diethylamino or dipropylamino, is in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentyl-methyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclo-butylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclo-propylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or is in each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy- or methoxy-carbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, and R 5 , R 6 , R 7  and R 8  independently of one another are hydrogen or methyl,   or a sodium, potassium, magnesium, calcium, ammonium-, C 1 -C 4 -alkyl-ammonium, di-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C 4 -alkyl)-ammonium, tetra-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C 4 -alkyl)-sulfonium, C 5 - or C 6- cycloalkyl-ammonium or di-(C 1 -C 2 -alkyl)-benzylammonium salt of this compound.   
   
   
       3 . The compound as claimed in  claim 1 , wherein
 R is fluorine, chlorine, bromine, is in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,   R 1  is fluorine, chlorine, bromine, or iodine, or is optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy or is dimethylamino,   R 2  is fluorine, chlorine, bromine, or iodine, or is optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy or is dimethylamino,   R 3  is methyl, ethyl, n- or i-propyl or cyclopropyl,   R 4  is methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, and   R 5 , R 6 , R 7  and R 8  are hydrogen,   or a sodium, potassium, magnesium, calcium, ammonium-, C 1 -C 4 -alkyl-ammonium, di-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C 4 -alkyl)-ammonium, tetra-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C 4 -alkyl)-sulfonium, C 5 - or C 6 -cycloalkyl-ammonium or di-(C 1 -C 2 -alkyl)-benzylammonium salt of a compound of the formula (I).   
   
   
       4 . A process for preparing compounds as claimed in  claim 1 , which comprises
 (a) reacting substituted aminoazines of the formula (II)   
     
       
         
         
             
             
         
       
       in which 
       A, R 1  and R 2  are as defined in  claim 1  and 
       Z is halogen, alkoxy or aryloxy 
       with thiophene derivatives of the formula (III) 
     
     
       
         
         
             
             
         
       
       in which 
       R and R 5  to R 8  are as defined in  claim 1 , 
       if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, 
       or (b) reacting substituted thiophene-3-sulfonamides of the formula (III) 
     
     
       
         
         
             
             
         
       
       in which R and R 5  to R 8  are as defined in  claim 1   
       with substituted triazolinones of the formula (IV) 
     
     
       
         
         
             
             
         
       
       in which 
       R 3  and R 4  are as defined in  claim 1  and 
       Z′ is halogen, alkoxy, aryloxy or arylalkoxy, 
       if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, 
       and, if appropriate, converting the compounds of the formula (I) obtained by process (a) or (b) by customary methods into salts. 
     
   
   
       5 . A method for controlling unwanted vegetation, which comprises allowing at least one compound as claimed in any of  claims 1  to  3  to act on unwanted plants, parts of plants and/or their habitat. 
   
   
       6 . The use of at least one compound as claimed in any of  claims 1  to  3  for controlling unwanted plants. 
   
   
       7 . A herbicidal composition, which comprises one or more compounds as claimed in any of  claims 1  to  3  and customary extenders and/or surfactants. 
   
   
       8 . A herbicidal composition, which comprises one or more compounds as claimed in any of  claims 1  to  3  and one or more other agrochemically active compounds. 
   
   
       9 . A compound of the formula (III) 
     
       
         
         
             
             
         
       
       in which 
       R and R 5  to R 8  are as defined in  claim 1 . 
     
   
   
       10 . The use of compounds of the formula (III) for preparing compounds as claimed in any of  claims 1  to  3 .